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Entrepreneur: Ryan Barr, founder of WhippingPost.com, a New York-based online
business that makes durable leather goods for musicians,
including a "picker's wallet" with a dedicated stitched pocket
for a guitar pick.

"Aha" moment: A musician with
an appreciation for vintage design, Barr was intrigued by leather
and the way it ages. In late 2010, after holding a series of
uninspiring jobs--including high-school history teacher and
medical-device salesperson--he started his business with a
collection of leather guitar cases styled after one he had
designed for himself.

"I'm more of a creative type, and I detest hospitals, so that
last job was not a very good place for me to be," Barr says. "In
a sense, it inspired me to work on this business so I could get
out."

He financed his dream the old-fashioned way. "I'd save some
money, buy some leather, make a prototype. Then I'd have to stop
and save some more. It was very piecemeal," he recalls. "I had to
make money to make progress." The cases got some attention from
trendy gear blogs, but a high price point--$825--meant a limited
customer base.

Pocket protection: In 2011 Barr decided to scale
down and market a more affordable product. "A lot of guitar
players shove picks between the credit cards inside their wallets
so that in case of a music emergency, they always have one," he
says. "I thought, I'll just make a wallet that has a separate
spot for it." Barr says he has sold about 4,000 of the wallets,
priced at $31 to $37, in the past year. Roughly 99 percent of his
business is done through his website, though a handful of U.S.
brick-and-mortar shops also carry the wallets.

Production process: On a recommendation (and
after he was able to save enough money to buy a plane ticket),
Barr visited a manufacturer in León, Mexico, that had a similar
aesthetic and desire for quality. "I've been using them ever
since," he says. "I spend a lot of time there. The tanners are
local, too, so I can pick out my product and have things made
quickly."

Tuning up: "I had a lot of concerns about
marketing," Barr says. "How do you get the word out about a
product no one is looking for?" He started by sending photos and
information to men's fashion and design blogs. First the men's
buying guide Uncrate.com, then Wired.com and other sites posted
about the wallets. His initial stock of 50 was gone within hours,
and Barr found himself scrambling to keep up with demand.

Solo act: Barr spent his first year in business
as a one-man show--designing the product, managing the website,
taking care of order fulfillment and everything in between. In
June he hired his first employee.

What's next: Whipping Post's first
non-music-related item, a $265 messenger bag inspired by vintage
postman satchels, was released at the end of the summer. Sales
were steady from the start, thanks to interest Barr drummed up by
documenting the design process on his site's blog.

"This is a crowded market--I'm not trying to fight the big boys,"
he says. "But unless you're buying attention with expensive
advertising, it's important to have a product remarkable enough
that people pay attention and talk about it." With this new
product, Barr is aiming for company revenue of $200,000 for 2012,
more than double the previous year's sales.